JPS6133013B2 - - Google Patents
Info
- Publication number
- JPS6133013B2 JPS6133013B2 JP53060518A JP6051878A JPS6133013B2 JP S6133013 B2 JPS6133013 B2 JP S6133013B2 JP 53060518 A JP53060518 A JP 53060518A JP 6051878 A JP6051878 A JP 6051878A JP S6133013 B2 JPS6133013 B2 JP S6133013B2
- Authority
- JP
- Japan
- Prior art keywords
- ubiquinol
- reaction
- ubiquinones
- silica gel
- calcium sulfate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 11
- 150000003669 ubiquinones Chemical class 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- TVLSKGDBUQMDPR-UHFFFAOYSA-N 2,3-Dimethoxy-5-methyl-6-(3-methyl-2-buten-1-yl)-1,4-benzenediol Chemical class COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC TVLSKGDBUQMDPR-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 8
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 229940040064 ubiquinol Drugs 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- PFIUSPPKANBDHQ-RJYQSXAYSA-N ubiquinol-7 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC PFIUSPPKANBDHQ-RJYQSXAYSA-N 0.000 description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 229940035936 ubiquinone Drugs 0.000 description 2
- DBESHHFMIFSNRV-RJYQSXAYSA-N ubiquinone-7 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O DBESHHFMIFSNRV-RJYQSXAYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- DSBZYDDWLLIJJS-UHFFFAOYSA-N ubiquinol-0 Chemical compound COC1=C(O)C=C(C)C(O)=C1OC DSBZYDDWLLIJJS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6051878A JPS54151932A (en) | 1978-05-19 | 1978-05-19 | Preparation of ubiquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6051878A JPS54151932A (en) | 1978-05-19 | 1978-05-19 | Preparation of ubiquinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54151932A JPS54151932A (en) | 1979-11-29 |
| JPS6133013B2 true JPS6133013B2 (enrdf_load_stackoverflow) | 1986-07-31 |
Family
ID=13144612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6051878A Granted JPS54151932A (en) | 1978-05-19 | 1978-05-19 | Preparation of ubiquinone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54151932A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918036A (en) * | 1984-08-16 | 1990-04-17 | W. R. Grace & Co.-Conn. | Cracking catalyst/sulfur oxide gettering agent compositions |
| US6461593B1 (en) * | 1992-02-19 | 2002-10-08 | Biomedical And Clinical Research | Therapy with coenzyme Q10 to reduce subgingival microorganisms in patients with periodontal disease |
| JP5060299B2 (ja) * | 2005-09-15 | 2012-10-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | キノン化合物の製造方法 |
| WO2007032378A1 (ja) * | 2005-09-15 | 2007-03-22 | Eisai R & D Management Co., Ltd. | キノン化合物の製造方法 |
| US7439402B2 (en) | 2005-09-15 | 2008-10-21 | Eisai R&D Management Co., Ltd. | Method for producing quinone compound |
-
1978
- 1978-05-19 JP JP6051878A patent/JPS54151932A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54151932A (en) | 1979-11-29 |
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